Barry was born in The Bronx, New York, and grew up in Florida. He graduated from the University of Florida with a degree in English in 1986. Before starting in stand-up comedy, he was a drummer in the indie rock band The Chant from 1984 to 1985. In 1999, his Comedy Central Presents aired. He wrote, directed and starred in the short film Borrowing Saffron (2002), co-starring H. Jon Benjamin. He has made guest appearances on shows like Dr. Katz, Professional Therapist, Home Movies, Space Ghost Coast to Coast, Wonder Showzen, Tom Goes to the Mayor, and Aqua Teen Hunger Force. He also voices a recurring character on Squidbillies. In 2004, he was featured in the animated series Shorties Watchin' Shorties. He made 16 appearances on Dr. Katz—in the first two, as himself; then as the recurring character of Todd, a video store clerk, in most of its final season episodes. He also played a character in the television pilot Saddle Rash along with Sarah Silverman, H. Jon Benjamin and Mitch Hedberg. In "The Third Conchord", the twelfth and final episode of the first season of Flight of the Conchords, Barry played Todd, a bongo-playing megalomaniac, who tries to introduce the song "Doggy Bounce" to the Conchords' repertoire, and a new band name: The Crazy Dogggz. In 2010, Barry had a recurring role as a fictionalized version of himself in the second season of the live-action Adult Swim series Delocated, where he played a frequent associate of the Russian mafia characters, casually playing card games with them in their club. He had a recurring role as himself in FX's Louie. Barry recorded the album Super Crazy on Comedy Central Records in 2012 . In 2014, he was featured wearing shorts on Season 3, Episode 4 of Jerry Seinfeld's web show Comedians in Cars Getting Coffee.